3-Hydroxybenzaldehyde

Chemical compound From Wikipedia, the free encyclopedia

3-Hydroxybenzaldehyde is an organic compound with the formula HOC6H4CHO. It is a colorless solid although most samples appear tan. Two other isomers of hydroxybenzaldehyde exist.

Quick facts Names, Identifiers ...
3-Hydroxybenzaldehyde
Names
Preferred IUPAC name
3-Hydroxybenzaldehyde
Other names
m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.630 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H checkY
    Key: IAVREABSGIHHMO-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
    Key: IAVREABSGIHHMO-UHFFFAOYAC
  • O=Cc1cc(O)ccc1
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearance colorless solid
Density 1.1179 g/cm3 (130 °C)[1]
Melting point 106 °C (223 °F; 379 K)[1]
Boiling point 240 °C (464 °F; 513 K)[1]
Acidity (pKa) 8.98 (25 °C)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.[3][4]

3-hydroxybenzyl-alcohol dehydrogenase is an nicotinamide adenine dinucleotide phosphate-dependent enzyme that produces 3-hydroxybenzaldehyde from 3-hydroxybenzyl alcohol.[5][6]

2D representation of the chemical structure of Q27102196.
3-hydroxybenzyl alcohol
+ NADP+
 
 
 
H+
Reversible left-right reaction arrow with minor forward product(s) to top right and minor reverse substrate(s) from bottom right
 
H+
 
2D representation of the chemical structure of Q2815988.
3-hydroxybenzaldehyde
+ NADPH
 

Biomedical properties

3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.[7] 3-Hydroxybenzaldehyde is used in the synthesis of monastrol.[8][9]

See also

References

Cited sources

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